Potassium Phosphate, Tribasic → 1-(4,4-Dimethylcyclohex-1-enyl)-4-methoxy-2-nitrobenzene

HRID 32132Notes

Reaction equation

HRID 32132 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[CH3:13][C:14]1([CH3:29])[CH2:19][CH2:18][C:17](B2OC(C)(C)C(C)(C)O2)=[CH:16][CH2:15]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[CH3:13][C:14]1([CH3:29])[CH2:19][CH2:18][C:17]([C:2]2[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=2[N+:10]([O-:12])=[O:11])=[CH:16][CH2:15]1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 792884-Bromo-3-nitroanisoleHCID 231420132-(4,4-Dimethylcyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 231415961-(4,4-Dimethylcyclohex-1-enyl)-4-methoxy-2-nitrobenzene

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a mixture of 4-bromo-3-nitroanisole (3.3 g, 14.1 mmol), 2-(4,4-dimethylcyclohex-1-enyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (4.0 g, 16.9 mmol) prepared in Example (1b), tripotassium phosphate (4.5 g, 21.3 mmol) and 1,2-dimethoxyethane (30 mL) was added tetrakis(triphenylphosphine)palladium(0) (0.82 g, 0.71 mmol) with stirring at room temperature under a nitrogen atmosphere. The mixture was then stirred at an external temperature of 80° C. for 24 hours.

Workup

  1. stirringThe mixture was then stirred at an external temperature of 80° C. for 24 hours

Sources & evidence

ORD record
ord-3548f23d5467419db4c84c79f61d3b2a
Source dataset
uspto-grants-2008_09
Patent number
US07425554B2

Reaction notes

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